


Like a Glove

by Jinngersnap



Category: Over the Garden Wall (Cartoon)
Genre: Other, Pegging, Strap-Ons, dominant play (light)
Language: English
Status: Completed
Published: 2015-01-12
Updated: 2015-01-12
Packaged: 2018-03-07 06:35:43
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 9,326
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3164909
Author URL: https://archiveofourown.org/users/Jinngersnap/pseuds/Jinngersnap
Summary: <blockquote class="userstuff">
              <p>((repost to new account!))<br/>A snow day and an early Christmas present lead do some… interesting outcomes. You bought that toy back in August, but only just now are getting the chance to use it… and Wirt is pretty down with the idea… (Made for a request I got for a reader wearing strap-ons...)</p>
            </blockquote>





	Like a Glove

**Author's Note:**

> QUICK NOTE: I know there’s a lot of debate about what era Wirt is from, if he’s a 60’s kid, 70’s (most likely…), or actual modern 2010+. But, because I am lazy, I am just putting this in the current year. 2k14. Wirt is just a lame vintage nerd.
> 
> Also, as per usual with most of my xReader fics, the reader is gender neutral, and DFAB (designated female at birth), so read this however you wish, friends.
> 
> OKAY LETS DO THIS

“I can’t believe they’re actually trying…”

You watched as Wirt swiped gloved fingers over the phone screen, the soft cotton making things unresponsive and slow to move. A warm smile came to you as he gave up trying to properly hang up his call, pressing the power button instead to send his phone into its screensaver. You heard a mumble come from him, a quick gripe about flip phones still being better than all the touchscreens taking over, and it only got your smile to widen. Wirt was the type to take an old fashioned Nokia over the fancy new trinkets. Durability and simplicity.

In fact, you were pretty sure the only reason he kept the newer phone was because of its ability to keep and record songs. Much easier than old cassette tapes.

You curled your knees to your chest - a tree sat behind you both, pine limbs keeping the floor a damp but snow free sitting space. Fresh falling snow had made the two of you seek refuge under the giant pine, but didn’t protect from the cold, soft puffs of warm air surrounding your heads as the two of you breathed.

“Was that your parents?” you asked, rubbing the palms of your hands against jeans, creating a little friction to warm them. Every year, you’d buy or receive a good pair of gloves… and every year, right before it snowed, you always seemed to misplace them.

“Yeah…” Wirt’s tone had a bit of a worried tone to it, though you suspected it was more akin to the fact that he was suddenly thrown with the responsibility of making sure Greg got home safe after playing with friends. “My- uh, dad, or…” he looked at you for a second, already knowing the whole  _‘step-dad, actually’_ speech would be lost on you, seeing as he had said it too many times already. He gave his bottom lip a quick bite before continuing; “He says that a bit of snow isn’t enough to keep him from a whole day’s pay. And since my mom’s work is nearby, they are just carpooling, sorta…”

With a shrug, he shoved his phone into a pocket, taking a moment to look towards the neighborhood. “Greg’s at Clarence’s place. His mom will call around dinner time, probably, that’s how it always goes. To see if he can stay for dinner. I probably don’t have to worry about then — though I didn’t ask if Greg  _could_  stay…” You watched as his eyes scanned over the snow, knowing that he was debating calling back…

“You probably shouldn’t call if your dad is driving.”

“R-right…” He gave a nod, “They’ll probably call later to check up, anyway…” a smile flashed your way then, and you couldn’t help but return it. In that moment, you had begun to pull your hands into your jacket, knowing that’d keep them a bit warmer, but the action was caught by Wirt. “Are your hands cold…?”

“It was a bad idea to try rolling a snowman with just socks on my hands…” Makeshift mittens never did work…

Wirt laughed though, glancing out into the nearby field at the lumpy and poor attempt at a snowman. Mix-matched rocks and twigs made the face and arms, and the entire thing looked like it could topple over at any second.

“We should wait until some kids come and ruin it, I wanna see it go down,” you said, looking towards it as well. “No one ever thinks to grab carrots when they leave the house on a snow day. I don’t think I even  _have_  any carrots at home.”

“I think we might.”

“It’s a little late now,” you laughed, turning attention back to Wirt. “But don’t worry. A bit cold, but it’s not like my fingers are going to fall off.

It got him to frown, suddenly sitting forward and twisting his body, facing you entirely. “Still, cold hands don’t feel good. Let me see them.”

“Wirt— that’s not necessary.” You weren’t even entirely sure what he was asking from you, but his waving hands made you turn and scoot closer without much thought, hands coming out from your jacket. “I’m fine, really.”

But he didn’t listen, maneuvering his gloves over your fingers now, but not stopping there - his own fingers moving against yours like inching caterpillars, until your palms were flesh with each other.

“There, see? Warm. Jeeze, your fingers are freezing, though…”

You stared down at your hands, bewildered for a moment before losing yourself in a fit of laughter. Two pairs of hands, stuffed inside only a single pair of gloves, and hand-to-hand like some Tarzan and Jane show off. “Oh my  _god,_ Wirt!”

“W-what…?” His cheeks brightened with a light blush, fingers giving a twitch against your own. “I thought…! I thought this was  _romantic_ , wasn’t it?” The words got only more snickers from you, getting Wirt to throw an embarrassed glare, “I just didn’t want you cold!”

A large grin spread across your face, hands pressing more into his. “I know,” you said, scooting closer across the damp ground until your knees were able to be pressed against his. “As dorky as this is, it’s sweet. Though… You’re going to stretch out your gloves.”

“It’s fine,” he said it quickly, words suddenly alert, like he was ecstatic he finally got your approval on ‘romantic’ gesture. “They are just cheap ones from the super market anyway— you know, the ones that are always on the racks near the cashier? Like, a few bucks, it’s fine, I can… buy new ones later…”

“I guess… I could buy you some, too.”

He smiled at that, “No, that’s alright. Besides, when in doubt, I could always just use a pair of socks, huh?”

Heat rose to your cheeks as a pout came, “It’s what my family has always done when we don’t have gloves!” He was the one to giggle at your words now. “It works when you’re desperate!”

He was only smiling, which got you to let out a small huff of air. But you couldn’t stay mad, not with your hands pressed against his in such a dorky manner, skin growing warm against his palms.

Words quieted down then, though both of you were smiling in the end, random cold brushes of air and snow from beyond the pine tree making you happy for the added warmth. Maybe it  _was_ a little romantic. Silly, and totally embarrassing if anyone saw. But… romantic.

“Hey, Wirt?”

“Hmm?”

“Do you think we could continue that conversation? The one before your parents called.”

It took a second, a sort of calm before the storm, until his face grew a quick dark shade of red, gaze shooting to you in a bout of panic. “W—… What?”

“We were busy talking, when your step dad called. Can we continue that?”

You could swear you felt his palms feel sweaty against yours, only in those couple seconds. He was stammering, no real words coming out, but the state of sudden panic in his demeanor was… amusing. Also, pretty damn cute on him.

“W-we…” words were finally beginning to form, “we weren’t…  _talking._ ” The last word was practically forced from his mouth, bringing another wide grin to your own.

“We weren’t?”

“N-… No. No we weren’t.”

Your fingers moved slowly against his. If they weren’t confined in the tight gloves, you’d try to lace his and your fingers together, but the small rubs would have to do for now. “What were we doing?”

Even with your eyes watching the gloved hands, you could  _hear_ his gulp. “We-… We were… ki—  _you_  were kissing… me…”

“ _That’s_ right!” you called out, faking your best act of recollection. “I totally forgot. Okay.  _That_. Can we continue that?”

There was a very obvious (and very red) pout on his lips now, and it only made you grin more. You didn’t wait for an answer, beginning to lean forward as he stammered and stuttered more, He quickly glanced out at the clear field, looking for people, watcher, voyeurs, eyes growing wide as your lips hit his and stayed against them.

It only took a few seconds before he closed his eyes, taking a deep breath and applying some pressure back into the kiss. But the kiss didn’t stay mutual for long, Wirt breaking it in a sudden fit of panic, looking out at the field again. “What— What if people  _come_  onto the field? They’ll see us— us  _kissing_  and holding hands. Oh god, what if we are labeled as exhibitionists? We could get fined with indecent exposure—“

“Wirt, I’m pretty sure that’s only if you’re naked—“

“or at least with a gratuitous public display of affection—“

“Can you even get nabbed with that…”

“Or what if some kids come and wreck the snowman like you wanted?”

“That’d be pretty awesome, honestly.”

He gave a groan, but you smiled, pulling your hands from the warm gloves and into the cold air (the fact that his sweaty palms had left yours wet only made the cold air more of a shock), but quickly laced your fingers against his. At least now you were able to get a grip on him, moving forward again as you laid a quick peck on his lips.

“Wirt.”

He only huffed.

“Just trust me for a second.”

You went slow, of course. You always went slowly with these things, testing waters, kissing him again in a slow and almost questioning way. It was only when you felt him breathe against you, hands gripping back and the pressure of him kissing back, did you actually begin your work. Simple kisses turned into lip bites, gripped hands turning into arms wrapping around his neck, hot breaths made even worse when mouths opened and your bodies moved close. Wirt was… easy to get warm. You knew his buttons, and you knew he not-so-secretly loved being the one to be kissed, and pinned down into the damp ground under a snowy pine tree.

And you would have kept him pinned, too, if it wasn’t for the distant laughter of a group of kids. He didn’t need to push you off - you shot off yourself, nearly growing lightheaded with the quick movement back onto your knees, Wirt following with a flushed face and wide eyes.

A group of kids, four of them, puffed up in their winter clothing and dragging a metal sled behind them. They laughed, threw crude snowballs, and - as soon as they saw it, ran to the snowman, shouted about how bad it looked, before throwing a set of snowballs at its face. Seconds later, the sled was being sped into it, bringing bellows of excitement and joy from the kids.

“That’s so awesome,” you breathed out, beaming with your own bit of excitement. Snowmen were nice and all, but the explosion of snow was one of the best things to see on a snow day. You were still smiling when you turned back to Wirt, who didn’t see so amused, looking to you with a blush so wide that even his ears were red.

“Oh come on, they didn’t see a thing,”

“How do we know…?”

“Uh, because they are  _kids_. If they saw anything, they’d be pointing it out and screaming about it.”

He gave a gruff sigh as he looked away from you, getting you to chuckle. “Come on, Wirt. You enjoyed that, and we didn’t get caught. I know a part of you enjoys that.”

“Enjoys  _what_.”

You could hear the hint of irritation in his voice, so you treaded carefully - you weren’t looking to make him  _mad_.

“You enjoy…” You ran your finger across his knee - the hand closest to the tree, unseen by any passing kids. “Being…  _beneath_  me, so to say.”

His reaction was beautiful, practically glowing crimson, contrasting perfectly against the white surroundings. He called out your name in a bit of shock, glancing to the others in the field, who weren’t paying either of you any mind at all. “Do—… Do you  _really_ have to say that sort of stuff?”

“It’s true, though.”

You heard his voice hitch, glaring at you, “Out  _here?”_

“So you’d rather me say it to you when we are alone?” You made sure to leave a bit of huskiness in your voice that time, obviously suggesting something, and making sure he caught on to it.

And he did, eyes scanning your face rapidly before his blush spread again. “I-i… You…” he was only stammering again, random words leaving his mouth as he tried to think of a good way to answer you.

“You know, your parents  _are_  gone for the day, and you don’t need to worry about Greg until dinner time…” There was true wonder in your voice then, only then coming to the realization that the two of you  _could_  be alone. You only got chances like that once in a blue moon, and even then, some of the chances were hushed and careful because of a sleeping or wandering sibling nearby.

In that moment, another idea sprang to your mind - one that you had been literally dreaming and fantasizing about since the moment a certain particular item showed up in the mail. You never had a proper chance to use it, not until…

“I could finally use that present I got you. It’s a little early, I guess… Early Christmas present…”

“Christmas is in just a few days— Wait.” Panic overtook his tone quickly, “present…? What did you buy…?”

You could tell he was connecting dots quickly - why else would you mention a present and private time in the same breath?

“Well, yeah. I mean, we were just talking about you beneath me—“ you ignored the way he quickly said your name in that warning tone, “and I can’t really try it out by myself. I mean… Not  _properly.”_

A long sigh came from Wirt, “What did you  _buy?”_

“Oh,” you gave a chuckle, “You know what it is. I mean, you were with me when I got it. Or, at least, beside me when I bought it online… You know, that nice one? It looks sorta real, too…”

Once again, similar to before, Wirt’s expression changed from one of confusion to sudden shock, grasping at words before he was finally able to form a few; “You—- you actually!! Online- I didn’t think… I didn’t think you…!”

“You were there when I was inputting my address, dude. We even discussed sizes like, all night.”

“I— I know, I know, I just…! I didn’t… I-I guess  I didn’t think you…  _actually_  ordered it, that was like… months ago!” He kept looking over to the kids, keeping his words simple and far from sounding naughty.

“Well yeah. I mean, it got to my house in like… September, Wirt. But I couldn’t just put it on and waltz over to your house—“

“Oh god—“

“So we had to wait. And…” You shrugged your shoulders slowly, giving him a small grin, an innocent and playful one, trying to show that you have  _really_  been wanting to try this, but also let him know that half this choice rested on his shoulders.

You didn’t rush him as he pressed his hands together, obviously nervous, gaze flicking across you and his surroundings as he thought. Eventually, he talked, low and getting red ears as he did; “I—… I have been thinking about it recently, I guess…”

“Have you…?”

He nodded, quiet for a few more moments before speaking again. “We- uh. We  _have_  been…  _preparing_. I just didn’t know you  _had_  one yet…!”

“Well…! Christmas present. But it’s not like we are presented with perfect openings all the time. So it’s not like I don’t mind giving it early. And besides, not like I can wrap it up and let you open it in front of your mom and—”

“No, no,” he held his hands up quickly, eyes shut. “Don’t finish that because I don’t even want to think about it.”

You grinned though, rubbing your hands on your legs in a bit of excitement. “Is…? Is that a yes? I mean- It doesn’t have to be a yes, believe me, don’t let me push you into thinking you  _need_  to…! There’s always more snow days and chances to be alone…”

“Yeah… but not a lot.”

“Not… a lot, yeah.” You began to bite your bottom lip just a little, afraid of him giving in just because of the timing. You watched him carefully, totally willing when it came to calling this off if it was too fast, or even suggesting a more simple ‘private time’, or just a more known and practiced type of alone time. It wasn’t as if either of you were virgins at this point; those barriers had already been broken down and explored way before this point. There was just the goal of having things the way both of you fantasized and hoped it’d be - hence buying the Christmas present in the first place.

But you still understood it could be scary - you were pretty damn scared once too.

“Let’s go to your house…”

His words surprised you at first - and then sent in a bit of confusion. “My house…? Wirt, my family is still home, we can’t—“

“No…! Of course not, but we… you… need to get it, put it in your backpack or something, c-… Come over… to my place. We can— I mean, I can walk you to your house, a-and…”

“Escort me back to your place…?” You finished, excitement welling up in your chest, though you tried your best to keep it there, not wanting to seem way too eager about the situation.

“Y-yeah…” he nodded, flushed face still very apparent.

“Are you sure…? I mean, totally, fully sure?”

This time, you got a smile, which got your heart to almost well in your throat. “Yeah,” he said, an actual tone of bravery there. “Yeah, I’m sure. Nervous, I think, but yeah…”

You let your own smile overtake you then, grabbing his hands and standing as fast as you could, bringing him with you and causing him to give a small yelp from the speed. Once standing, you ran your hands across your legs and behind to get the twigs, grass, and other things off your pants. “Okay. Okay, let’s go. If we are fast, that just means we have even more time to take things slow, right?”

“R-… Right!”

* * *

 

Your family didn’t even raise an eyebrow to you running inside and then running back out with your school bag strung around your shoulder. You had planned to just tell them that you wanted your school books with you, for a project with Wirt. It was a pretty overused excuse, but it would have worked.

And you  _did,_ in fact, have a project with Wirt. Just a project that had nothing to do with text books. Maybe, if you had a few text books about anatomy. But you wouldn’t be starting Health class until next semester.

You walked, happily, arms linked with Wirt. Every now and then, you’d press the side of your head against his shoulder, an act that always got him to mumble nervously. You were… happy. Excited, sure, in more ways than one. But excited mostly with the knowledge that Wirt had previously said that this was something that  _he too_  had been thinking about.

Sure, the two of you would talk about it a lot. Normally talks that’d end in hushed moments of not being able to make noise, locked away in his or your room, constantly checking for sounds from siblings and parents. You knew that  _you_  thought about it a lot. Hell, you had the item in your possession for months now, quietly dreaming of the chance you’d get to wear it and actually show it off, not just fantasize.

But the fact that Wirt had thought about it too. Maybe fantasized about it. Maybe even got flustered and excited by the idea. And, most of all, maybe he actually  _did things_  because of his thoughts. That was what got you the most. The thought of Wirt doing anything to himself with you being in mind… it brought a blushing smile to your face.

You tried asking Wirt, even. And he made it pretty apparent that he  _did_ , flushing a dark red and huffing out your name with a squeaking voice. You didn’t push the subject - that was proof enough. If you pushed too much, it’d only make him mad. It was a lot easier, and more worth your while, to throw a few teases at him when you were actually alone.

Neither of you wasted time in his living room, closing the front door (locking it, even), heading upstairs without saying any words at all. You could tell Wirt was beginning to get eager about all this as well, since the trek upstairs had him almost tugging you along, bringing you into his room and closing his door quickly, clicking the lock closed and taking a deep breath before he turned to face you.

You could tell he was nervous, hands clenching as he scanned you, looking for words, though not managing to even say a single thing. It made you chuckle, walking to him and taking those nervous hands, leaning forward to kiss lips softly. “You still feeling up to this…?”

“Y-yeah…” he didn’t leave your mouth, but didn’t kiss back either, only letting his breath hit your lips. Soft fingers - gloves having been shed when coming inside - ran tenderly across your jawline, and you could see his eyes carefully watching you. Still though, he was silent.

His nervousness was cute - but something you wanted to cure as well, tossing your backpack to the bottom of his bed, looking back as it slid from the edge and met with the floor. “Don’t think about that stuff right now. We can focus on… other things.”

“Other… things?” There was a crack in his voice, as his hands went to loosen the collar of his shirt. “You mean like…?”

“I just mean like…” you took his hands away from his collar, leading him towards the bed. You didn’t need to coax him to sit - these were all motions you two had done before. Familiar territory. “Doing stuff we have already done. Just a… ‘normal’ night between us. Or, well… a normal  _private_  night.” A chuckle came from you as you sat next to him -  _normal_  nights were just ones spent trying to introduce him to video games, or him trying to introduce  _you_  to old vinyl records. Normal  _private_  nights had… different outcomes entirely.

You could tell he was already becoming less tense already, shoulders relaxing as you laid simple kisses along his jawline. He even began to kiss you back, not even flinching as your hands laid on his knees, began to explore… This was the norm, after all. Calm, almost relaxing kisses, carefree and totally welcomed touches. You hoped he wasn’t thinking about the toy in your bag - or, if he was, that he was becoming less scared of it.

As usual, he gladly let you move atop him, pushing him down onto pillows as the two of you rearranged to be entirely on the bed, sitting on his hips as the kisses turned more hungry, more…  _wet_  was a good word, maybe. It amazed you how easily Wirt fell into a sense of not caring… the same guy who normally fretted over simple things, so effortlessly losing himself amidst kisses and touches. In fact, even more, it amazed you how easily you were able to make his breath grow heavy, and eyes grow fogged and needy.

It may, or may not have, been something you were quite proud of. Okay… You were really damn proud of it. A few minutes of kissing and nibbling, and curious careful hands touching only hips, torso, and outer thighs, and you could already tell his body was hot. Red and sweating, breath heavy as hips moved into your own in a silent beg to stop touching the less sensitive bits of his body.

You liked the silent begs - but they weren’t as beautiful as the times he’d actually use his voice. Whines were one thing… but actually asking.  _That_ … that was something that got you going, even when Wirt was nowhere nearby. Many sleepless nights were spent thinking about the way his voice would crack when he cried out for you to  _touch_  him.

It was quickly figured out that you were the more dominant one between the two of you. Which seemed to work out perfectly, because while you enjoyed pinning the boy to the bed, Wirt was always glad to be the one pinned. Which sparked the conversations about the special item in your bag - something that both of you seemed excited about, and a feat that needed its points of preparation. There was no way you were going to use it on him without getting him accustomed first.

More clothes were being shed, though not all, shirts staying while coats and sweaters hit the ground, bodies picking up to be able to begin to grab at pants. Hands moved frantically at this point, not much care in the matter, kisses still happening but sloppily as it was getting hard to keep mouths together. Wirt had gotten your own pants off first, though mostly only because of the ease of removal with you being on top of his hips -  but a shift of his own let you tug his down, pushing them from the bed and out of the way.

His boxers made it apparent how much the heated kissing had affected him - a tent that he knew better now than to cover or become shy of. Instead, he glanced at it for a moment, gulping down a few nerves as he looked up to you - not saying a thing but telling you exactly what he wanted.

A silent beg that brought a smile to you, running your fingers softly upwards along his inner thigh, an action that made his breath hitch as he lay back onto his elbows. You knew he was watching you, which only raised your ego slightly, and strengthening the urge to tease and fluster him even more.

Which you did - grip tightening as it stayed only on his inner thighs, giving occasional pinches and light scratches, until he finally began rolling his hips towards your hand. You responded by tugging his boxers by the waist, making sure to hesitate right over his groin, enough to catch his length in the band of the boxers. When you finally pulled down far enough, it caused his length to flick hard against his stomach, making him gasp.

You gasped, too, though it was in total awe - the loving kind that made you bite your bottom lip in a smile. He was cute, even this part of him, though he hated when you used such words to describe him. You couldn’t help it sometimes, looking down at him with a very excited (and rather cute, in your honest opinion) dick, nearly pressing into his lower stomach, yearning to be touched. And be touched by  _you._  That always got you the most.

He knew better than to touch himself, too. You’d never…  _punish_ him, persay (unless he wanted that), but all you needed to do was give him a ‘not yet’ or ‘not allowed’, and he’d grip his fingers into the bedsheets instead. Even now, he didn’t bother trying, automatically clutching at the blanket beneath him as he watched you. As your hand neared his groin, you saw his length twitch slowly in the anticipation of being touched, and his breathing even grew louder as you were only centimeters away.

When you fully took him into your hand, he finally made an actual noise, just a squeak of his voice as he gasped outwards, and a glance upwards showed you that he had closed his eyes. It made you smirk again, not hesitating to begin a pace with your hand, enjoying every sound he made afterwards, and even more so enjoying the way his hips would give small thrusts upwards.

You liked to think that you were pretty good at this, or at least getting there. Your fingers knew all the key points, where to touch, where to focus on. Even how hard to grip and which speeds Wirt liked the best, or all the perfect times to take a moment to run your fingers across the tip, collecting the bits of pre to make the pumping easier. It didn’t take long at all for Wirt to really begin squirming beneath you, whimpering whenever you suddenly changed pace speed, or took a moment to slow down.

You had a system for this - a few key things to look for before you would actually continue. The hip rolling was one of them, as was the small noises and gripping of the sheets. But the last thing, and most needed to continue, was the small (barely audible) noise that just hit your ears - your name, hummed from his lips as his breathing grew faster. It was permission to press forward, as well as a warning… He was getting close, so a change was needed.

Even though he basically asked you to stop, he still gave a small groan when your hand halted, a noise that got you to giggle and give the smallest of pinches to his thigh. “Nerd, do you still have some stuff left?”

It took him a second to answer, catching his breath as he pushed himself into a sitting position, and turning from you to dig into his bedside table. Seconds later, he placed the small container in your hands, and in thanks you placed a small kiss on the still panting lips. You could tell he was attempting to kiss back, pressing forward and continuing to give small moans directly in to you. You found yourself smiling into the kiss, chuckling even, letting the kiss linger before pressing lightly on his chest - a gesture he listened to quickly, laying back fully until his head rested on pillows, half lidded eyes watching you as you worked the small bottle open.

Wirt had already begun to rearrange his hips slowly, legs soon draped over your knees. You knew a bit of lube went a very long way, but there was never such thing as too much in these times, so you let the clear liquid drip onto fingers and - before it could drip onto the bed - brought your fingers close to the small entrance.

It got a gasp from him, one you immediately stalled at. “You okay…?” He shouldn’t have felt much at all at that point, but you knew that he knew his body a lot better than you.

“It’s-…” He had to swallow, finding his voice, “N-no— I mean yes! I’m fine! Just… Sheesh, that’s always so cold…”

“Oh…” a chuckle left you, “S-sorry, I always forget that… We should keep it inside a pocket before we do this stuff, maybe.”

“That’d take…a lot more planning…” He shifted his hips against your fingers, and you felt him essentially begin to press against them, watching as he gave a small gasp at your fingers just beginning to enter.

You could tell that conversation wasn’t exactly wanted at the moment, and grinned silently to yourself. After a small lean forward, followed by a chaste kiss, you moved back up to sit on your heels as your fingers began to actually play.

This wasn’t new territory. It was far from the first time that the two of you had done something like this, so it took barely any time at all for you to easily add a second finger inside him, an easy and quick going pace that made his hips rock back onto your fingers. He liked it - loved it even - something you’d normally mention out loud - small teasings that’d get him even harder and moving faster against you.

Of course, you’d normally stop at two fingers. Begin to stroke him, bring him to his peak quickly with curved fingers that have managed to, sometimes, actually find the prostate and  _really_  make him moan. You weren’t perfectly skilled at honing in on the little button, but you had gotten better, and his noises made it worth all the effort.

But this time, you had a goal in mind - and he seemed to know this as well, giving a small wince but not questioning when you added the third finger. You could  _tell_  it must have felt bigger to him, since it felt tighter to  _you,_ still easy goings (thanks to the gratuitous amounts of lubrications), but a lot tighter. You broke from your normal power-top routine, leaning down to shower his jawline and lips in small kisses, free hand rubbing his legs, thighs, and even length in a few quick movements. You knew this could feel good, you knew he could feel amazing - it was just the process of growing accustom…

It took longer than usual, of course, but he still began to rock against you, groaning even louder now, hips grinding and teeth lazily grazing your neck and jawline. He was already at the point of clinging to your arms and shoulders, whining against you, making your own body feel suddenly  _very_  hot, nearly to the point of exploding.

You stopped moving your hand - making sure your fingers were deep when you did so, a gesture that got him to groan and try to continue the motions himself with rocking hips. But you didn’t move, instead nuzzling below his ear, finding yourself panting with pure need at this point.

“Wirt…” just saying his name got him to gasp - totally stopping his hip movement but whining softly as he did so. You tried to run your hand down his body again, under his shirt and dragging nails, hoping it’d suffice for the muted movements of your fingers inside him. “I need…” A single chuckle left you, almost a huff, amused by the words wanting to leave you, but not embarrassed by them at all, “Wirt, I—… I  _really_  need… to be  _inside_  you…. actually, fully inside you.”

The noise that game from him was close to a startled grunt, shaking as he breathed out. “D-don’t…” It was his turn to give a chuckle, though his was coated with nerves. “Don’t say things like that, I’ll… I’ll co-co—… I’ll  _go off_  without you even moving…!”

Somehow, that only boosted your confidence even more so, grinning against his skin.

“You’d do what?”

“G-…  _go_ , I’d uh. Finish, you know.”

“Hmm,” you hummed with a smile, leaving a small trail of kisses across his jawline. “I don’t know. You should just say it.”

He gave a small groan - Wirt already  _rarely_  talked dirty, but when you asked him for it, it only embarrassed him more. Like it was putting emphasis on a word, which only made it more awkward to blurt it out.

Which made getting him to say it a lot more fun. And, more often than not, the word wasn’t even anything explicitly naughty. Wirt just made it seem that way.

“What would it make you do?” you hummed out, still leaving small kisses as your fingers moved just  _slightly_ , enough to get him to groan. Your name even left his lips, a small whine breaking the syllables apart.

“Hmm?” your fingers began to curl now, looking for the special button once more. When his body shook with a jolt, you knew you had found it, beaming as you continued to massage the bundle of nerves. “What would it do, hmm? Me talking about being inside you? I could finally  _fill_  you up, Wirt.”

The gasp that came from him was  _loud_ , making you more than happy that the house was empty. “I…!! Okay, I—!!” His hips tore away from your hands quickly, and you took it as a sign of being  _too_  close, nearly making him ‘go off’, to use his choice of wording. “C-come!” It blurted out, followed by a groan, but he didn’t stop there. “I-I’d come, okay?! I’d c-come hard— r-really fast, so…!”

You bit your lip in your smile again, taking it as your winning trophy and pulling your fingers from him, enticing an almost silent whimper from Wirt. “Alright, alright. I’m actually surprised you didn’t already, the way you were clenching my fingers near the end there.”

Your words got you a glare, so you smiled softly, leaning forward to give a quick kiss. “Sorry. I’m… Really excited.

“I can tell.” There was an air of annoyance in his throat, but it disappeared after he gave a small kiss back. “It’s okay, I-…. I am, too.” The grin he gave you could only be classified as goofy. Maybe a hint of nervousness in there, but mostly goofy, and a smile you couldn’t help but kiss, smiling into it yourself.

“Can I…?” You weren’t totally sure how to ask if it was okay to continue, but you knew he’d understand the meaning regardless. You were hoping for a yes, god you were hoping, but you were still prepared for the suggestion of waiting a bit. You didn’t fully mind - the two of you could just as easily reach a point of getting off with you riding Wirt (or the few occasions where he had the urge to actually control from the top, though you strongly considered yourself a power-bottom in those moments), but you still held high hopes…

Hopes that welled up in your chest when you saw him give a small nod. “Y-…” he paused to clear his throat, “Yeah, I… I want you-…” he stopped, and you guessed he realized that he was about to say something pretty lewd, and the way he met your eyes confirmed that.

“Inside?” you questioned, grinning at the pout he gave you.

“J-just…! Go slip it… on, or strap it on? D-do you need help?”

“I’ve got this,” you blurted quickly, pecking him before moving off of the bed in nearly a single fluid motion, hurrying to the bag that had fallen before. “I’ve tried it on before, to make sure things were going to fit alright.”

“O-oh… and?”

“Fits like a glove,” you said it while standing, pulling the main event from your backpack. Simple - not super expensive or anything, but still a few good pretty pennies went into the purchase. Your favorite color (it was yours, anyway!), complete with strategically placed straps and fasteners. And, of course, the ‘realistic’ member jutting out from the front. A rather nice dick, you considered, not very big but good for ‘beginners’, as the internet kept telling you.  There were more expensive ones that spoke about ‘life like’ feels, but this one seemed just perfect for now. A good size. A color that matched your skin tone. Even sort of cute. It was a cute dick.

Cute dicks were very important.

Wirt must have liked it too, since you heard a small ‘wow’ come from him.

“Nice, right?”

“Was that the one we were looking at…? It seems… bigger, up close.”

“This is like, the smallest size. Well, of dong, at least. Six inches, I think? Yeah.” You chuckled, stepping out of underwear with little shame at all, noting for a moment at how wet they seemed, but not drawing any attention to that.

Though, you did turn to Wirt, giving him a quick nod, “turn around for a second.”

He gave a small blink to the request, but listened without much of a fight, turning his torso slightly and even covering his eyes with hands. With a smile, you began the process of actually putting the contraption on - something that was confusing at first, but you could do pretty quickly now. There was even a little treat, for you, tucked neatly into the front. A ‘bullet’, pressed directly into your most sensitive bits, but not turned on just yet. That would be for a little later.

Once completed, you let your shirt fall over the toy just a bit - a button-up that parted near the bottom, framing the semi-realistic toy, and… giving just a little air of authenticity. “Okay…” You said it with just a hint of nerves - feeling fantastic with the view, but hoping that Wirt wouldn’t find it silly. “You can turn around…”

He didn’t say anything at first, staring, mouth slightly agape as he looked you over. The silence was getting you nervous, and fast, your hands shooting down to play with the hem of the shirt, hoping things actually looked  _okay_.

“Wirt…!”

His eyes met yours in a bit of panic, shaking his head quickly as he scooted forward, “S-sorry! Sorry, I…! I… Wow…” he swung his knees over the bed, which made him just close enough to reach out and touch just the tip of the toy. “It looks amazing on you… Really, it does!”

The smile he gave quickly gave that confidence boost you needed in that moment, and when his hands, reached for your hips, you gladly took a few steps forward. You returned his smile now, his hands lying on your hips while he was…  _very_  close to the new toy, enough so that he could - and did - run his fingers across it from base to tip, running along the ‘realistic’ veins and details.

“It’s nice…” his voice had grown lower, huskier, hand still examining it while his other made small ghosting touches down your thigh. “I-it… can’t go in  _dry_ , though.”

You were a little taken back by Wirt saying anything slightly naughty, but tried to shrug it off anyway, “Of course not. That’s why we have lub—“

Your words were cut when you saw Wirt move forward, doing something that - quite honestly - surprised you for the first time in a  _long_  while. His eyes half lidded, mouth opening wide as his tongue ran across the tip of the length ( _your_  length, you wanted to call it here), making you gasp and want to sink a hand into his hair.

But you didn’t, instead bringing them up to cover your mouth, watching silently as Wirt moved his tongue in ways you could only guess he learned from  _you_. Even without nerve endings in the toy, it was somehow just as erotic to watch the display, moaning into your hands as Wirt even managed to take the length  _into_  his mouth. In that moment, you did let your hand tangle into his hair, tugging just slightly and getting him to groan; a vibration you couldn’t feel physically, but your brain somehow understood how  amazing it would feel.

“Wirt…” You wanted it to continue, you wanted to watch him to that all night - but there were so many other pressing matters at the moment. Most of all: you needed, really needed, to fuck him. You didn’t care about word usage, or that it sounded dirty. You needed to pin him, pound him into the mattress, make him call out your name, scream it, beg with your name on his lips…

All things you needed, and all things that you were able to convey in that single time you said his name. He met your eyes for just a moment before nodding, moving back onto the bed, arms wrapping around you as you followed and tangled your limbs into his own. Kissing at this point was sloppier than ever, mouths barely matching as bodies kept moving, grinding against each over as legs moved into the positions they needed to be.

With a loud series of pants, you pushed Wirt by his shoulders, pinning him to the bed and staring down at him. The look he gave you must have been pretty similar to yours - red, sweaty, eyebrows knitted together as bodies rocked.

Similar to before, both of you worked to have Wirt’s legs draped over your knees, and you slowly ran a hand over your length as you sat back on your heels. Not as wet as it needed to be, though spit never did much. A few quick pats to the bedding got you the lube again, and you wasted no time in coating the member, gulping as you looked down at Wirt. He was staring up at you - eyes somehow trusting, chest moving heavily with pants that still wrecked his body.

You gave him a nod before moving forward, hand directing the length where it needed to be, giving his leg a small squeeze as you began to give more pressure. His breathing had hitched, just slightly; you could hear it just barely through your own heavy panting. But you knew this would take a bit more force, just enough and it’d be in, and then things could go slow, gentle, until he was fully ready…

More pressure, just a little, and you could swear you heard it when you finally pushed inside, gasping yourself at how deep you seemed to go just on the first try. Immediately, you looked up to Wirt, afraid to see him in pain. And - while he seemed to be  _very_  aware of the invading object, he didn’t seem to be in a great amount of discomfort.

“Are you…? Okay?”

He only answered with a small nod at first, hips rearranging slightly around you, even trying to twist his torso a little. “B-… Bigger.”

“Too big…?” It was the smallest you could find, but you had the sudden regret of not looking more, knowing there had to be smaller ones, easier ones…

But he shook his head quickly, “N-no! No, it’s… It’s okay, not too big… Just… wow.” A small laugh left his lips, getting rid of a few of the nerves that showed on his face, “I’m fine, really. I… want this, too.” The way he smiled afterwards nearly got your heart to flutter, and you gave him a nod - you’d make sure this was good. Good enough that it could become the norm, good enough that both of you wanted this again and again.

The pace you began was slow, careful, going in until your hips were flesh with his skin and bringing small soft mewls from him, before pulling back out and enticing a noise from both of you. It was somehow super intense, despite the lack of nerves, and in the moment that didn’t even  _matter_. Because Wirt was beginning to react in good, squirming ways that he only did on your fingers, now so much more intense with the new bigger size.  

Your hips rolled forward with a bit more gusto now, trying to really grind, trying to feel more of him, when you remembered the small bonus gift that the strap-on provided. You pulled out just half way, giving a small “hold on…” as you pushed your shirt aside, digging into the front part of the strap-on.

Wirt was quick to sit up on elbows, watching in confusion, but once the small buzzing sound started - followed by a surprised laugh from you, he gave a chuckle. “Is that…?”

“Y-yeah…” It felt… good, though not strong exactly just yet, but enough to make your knees shake just a little.

“Good…” Wirt moved to lie back down, hips giving a small push into yours to bury the toy a little deeper. “I was… a little afraid you wouldn’t get much out of this…”

You shook your head as soon as he said it, shuffling your knees slightly as you took his hips in your hands, “I would have enjoyed this no matter what… this is just a tiny bonus…” you didn’t hesitate now, pressing deep, getting a groan from Wirt but calling out yourself this time. Burying deep caused the vibrating bullet to move against you in just the right way, just for a moment. You quickly wanted more, pulling out with a slight slow movement before quickly thrusting back in.

Once again, an intense burst of vibrations, made a million times more magical when Wirt’s body arched at the harsher thrust, crying out a shaking moan. Again - you did it again, and once more after that, a pace quickly taking hold with the slower out motion and the harsh, quick thrust inwards. Wirt’s hands grasped at your wrists that held his hips, nails digging but hips gladly rocking into each and every hard shove forwards, not to mention the sounds that were coming from him.

The sounds you loved  _a lot_. Ones that came only a few times in previous sessions, but this time, each time you moved, he was moaning for you. Calling out, voice cracking, murmuring your name in a voice broken with panting and heavy gasps.

It wasn’t long before you changed that pace, letting go of his hips to lean onto your hands, placed at his sides. Fingers dug into the bedding while Wirt’s hands wrapped around your frame, sinking under clothing and clutching at skin. The pace now had no slow points at all, quick with each movement you made, hips rocking in a speed that you  _knew_  would throw you both over the edge in seconds.

You could hear the way Wirt’s moans were shaking, and you knew he was close. Holding your weight on one hand, your other moved to his own length, grasping it without much warning and quickly pumping it, a frantic pace that didn’t much match the one you were making with your hips. But Wirt didn’t care - he didn’t complain at all, chest arching forward as a loud groan over took him, a noise that didn’t stop or lower in volume, only grew with each breath as you rocked him over the edge.

You had learned, though experience of course, the types of moans Wirt gave when he came - the loud, whimpering ones that you normally had to shut up with kisses. But this time, you let him call out, feeling your pumping hand grow wetter as you continued to squeeze gently, getting him to give every last shaking drop.

Your hips, however, didn’t stop moving. It only made Wirt moan more, a tired and broken moan that you moved in to kiss, closing your mouths together as you focused fully on grinding deep inside him, pressing your groin against the vibrations, twisting and rolling your hips until the wound up coil inside you finally released. It made you break the kiss, gasping loud into Wirt’s mouth, nearly crying as the strong waves took over, more intense now with the still constant vibrations making everything feel almost electric.

It lasted a good while - at least longer than usual. Or, it felt that way. Eventually the tightness in your muscles finally left, leaving you to lean up and backwards, hand quickly sinking into the strap on to take the bullet and turn it off, body  _way_  too sensitive to have more vibrations now that orgasms had happened. With the bullet off, though, you didn’t care much about removing the bit entirely, instead sufficing with removing the length from Wirt (an action that got a small moan from him) before simply tossing yourself to lay beside him, panting as you stared up at the ceiling.

It was still light outside - you only just now paid attention to this, a small oddity compared to the fact that all previous endeavors happened secretly and at darker hours. It got you to chuckle, the thought of the two of you using a snow day to sneak away and do such things.

“What…?” the laugh must have piqued Wirt’s interest, since he was turning to his side right afterwards, staring with eyes that may have seemed tired, but no longer fogged over with blatant horniness.

You shook your head, turning to your side as well, cuddling into his arms without any real thought in the manner. “That was just really nice.”

Arms moved around you softly, a chin resting above your head. “It…  _was_  actually.”

“You liked it…?” It was a silly question, maybe, considering how much he was moaning and whimpering during the whole thing, but some validation was always nice.

The question must have embarrassed him just a bit, since you heard him begin to stammer, “I-i… Well, yes… I did…”

Pulling away, you looked at him head-on now, eye to eye, trying to read his expression. “You did…? So, we can… do that again, yeah?”

You could see the blush on him grow, but when he nodded, it seemed truly genuine. “Y-yeah… I’d like that, I think? I feel, uh… maybe, a little sore? Right now, I guess. But that’s… normal?”

You gave a tilt to your head as you pondered it, “Well, I mean, people always talk about being a little sore… So I guess  _some_  is normal. I did get… a little rough there, I think…”

Wirt gave a pout now, “Yeah, you did…!”

“But you seemed to enjoy it…”

“Y-yeah….” a deeper blush, “I…  _did_.”

A smile overtook you now, leaning forward to peck him softly. “Good.” Once again, you moved into his arms, sighing happily when his arms moved around you. You could feel the strap on pressing into his body, but felt little care for it at the moment - it was almost a nice reminder of the day’s events. A good ending to a good, snowy day.

“Oh-…” though, speaking of the day ending, you looked up at Wirt one last time. “Dude, don’t you need to call to check up on Greg?”

The groan that came from Wirt was almost as loud as the ones from before - the only difference now was the tone, Wirt rolling over onto his back as he rubbed his forehead. “Either way, we are going to have to get dressed to go pick him up.”

A small chuckle left your lips. “Oh man. Make sure you don’t walk weird, everyone will know.”

He sat up as he looked at you - making you sit up too, raising an eyebrow to the shocked face he was giving.

“Do you…? Think they would? N-notice, I mean…”

You opened your mouth to answer, ready to laugh at Wirt taking things way too literally, but the ringing of a cellphone quickly shut you up. It was Wirt’s ringtone, making the boy shuffle across the bed and dig around for discarded pants. Once found, he dug into a pocket, mumbling a small “speak of the devil” after looking at the screen. A peek from you showed that it was Clarence’s mother, most likely calling about to ask about dinner.

You grinned widely as Wirt answered, his voice polite as he talked, and you slid off the bed to remove the strap on and shove it back into your bag. You figured… it was a good idea to clean the toy, since every website ever talked about proper cleaning techniques, but washing it in Wirt’s house seemed almost dangerous.

Eventually, you turned to face Wirt once the call was over, throwing on your pants as you spoke; “Are we picking him up?”

“No, I guess they called my mom? A-at work, I mean. He’s staying for dinner, but we have to pick him up in an hour…”

“An hour… Not enough time for another round?”

His flush was back, as well as the stammer, but you quickly shook your head and snickered, “I’m kidding, I’m already dressed. Also I want food.”

Wirt gave a huff now, legs swinging off the bed, “Food?”

“Yes. I’m hungry. Let’s go make food, we need dinner too you know.” You grinned at him, walking over to take his hands and pull him up to stand. “Come on. I’ll cook. I’m sure you’re  _sore_  anyway, no need to stand and over exert yourself!” It earned you a small groan and a glare, but you chuckled all the same.

Wirt, in the end, was still fun to pick on. Especially when it ended like  _that._


End file.
